7664-66-6

Basic information

• Product Name: 4-Isopropoxyaniline
• Synonyms: P-ISOPROPOXYANILINE;AKOS BC-2569;AKOS BBB/094;4-ISOPROPOXYANILINE;4-ISOPROPOXYBENZENAMINE;4-ISOPROPOXY-PHENYLAMINE;4-ISOPROPOXYLANILINE;4-ISOPROPYLOXYANILINE
• CAS NO: 7664-66-6
• Molecular Formula: C9H13NO
• Molecular Weight: 151.21
• EINECS: 231-636-9
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 7664-66-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 244 °C (decomp)
• Boiling Point: 95°C 0,4mm
• Flash Point: 110.6°C
• Appearance: /
• Density: 1.03
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: 1.5430-1.5470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.15±0.10(Predicted)
• CAS DataBase Reference: 4-Isopropoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropoxyaniline(7664-66-6)
• EPA Substance Registry System: 4-Isopropoxyaniline(7664-66-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 7664-66-6(Hazardous Substances Data)

Usage

General Description

4-Isopropoxyaniline is an organic compound with the chemical formula C9H13NO. It is a substituted aniline, meaning it contains a benzene ring with an amino group and a methoxy group attached to it. 4-Isopropoxyaniline is commonly used as an intermediate in the synthesis of various drugs and agrochemicals. It is also used as a reagent in organic chemistry reactions, particularly in the formation of carbon-nitrogen bonds. 4-Isopropoxyaniline is a clear to pale yellow liquid with a slightly aromatic odor. It is considered to be a hazardous substance and should be handled with caution due to its potential health and environmental risks.

InChI:InChI=1/C9H13NO/c1-7(2)11-9-5-3-8(10)4-6-9/h3-7H,10H2,1-2H3

Upstream product

• 26455-31-2 1-isopropoxy-4-nitrobenzene 
• 1693-39-6 N-(4-hydroxyphenyl)formamide 
• 75-26-3 isopropyl bromide 
• 100-02-7 4-nitro-phenol 
• 135049-82-0 1-iodo-4-(propan-2-yloxy)benzene 
• 6967-88-0 1-bromo-4-isopropoxybenzene 
• 683-60-3 sodium isopropylate 
• 540-37-4 p-aminoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 106-47-8 4-chloro-aniline 
• 73010-54-5 4-isopropoxy-4-methoxycyclohexa-2,5-dien-1-one 
• 150-76-5 4-methoxy-phenol 
• 622-62-8 4-Ethoxyphenol 
• 7495-77-4 4-isopropoxyphenol 

Downstream Products

• 84308-86-1 N-(2-isopropoxy-phenyl)-N'-(4-isopropoxy-phenyl)-acetamidine 
• 100129-54-2 N-Chloracetyl-4-isopropyloxy-anilin 
• 87672-31-9 N-(4-Isopropoxy-phenyl)-isonicotinamidine 
• 88827-79-6 3-(4-Isopropyloxy-anilino)-2-methyl-α-naphthochinon 
• 84308-89-4 N-(4-isopropoxy-phenyl)-N'-[2]naphthyl-acetamidine 
• 84308-83-8 N,N'-bis-(4-isopropoxy-phenyl)-acetamidine 
• 947240-29-1 N-(4-isopropoxyphenyl)-2-bromoacetamide 
• 1180153-52-9 (4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine 
• 1178881-74-7 (+/-)-1-(butylsulfonyl)-N-[4-(propan-2-yloxy)phenyl]piperidine-3-carboxamide 
• 1235467-28-3 3',4'-dichloro-4-(4-isopropoxyphenylamino)biphenyl-3-carbonitrile 
• 916666-98-3 4-(6-amino-5-formyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid (4-isopropoxy-phenyl)-amide 

Relevant articles and documents

Crystallography-guided discovery of carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators: insights into different protein behaviors with “short” and “long” inverse agonists

A series of 6-substituted carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators were discovered through 6-position modification guided by insights from the crystallographic profiles of the “short” inverse agonist 6. With the increase in the size of the 6-position substituents, the “short” inverse agonist 6 first reversed its function to agonists and then to “long” inverse agonists. The cocrystal structures of RORγt complexed with the representative “short” inverse agonist 6 (PDB: 6LOB), the agonist 7d (PDB: 6LOA) and the “long” inverse agonist 7h (PDB: 6LO9) were revealed by X-ray analysis. However, minor differences were found in the binding modes of “short” inverse agonist 6 and “long” inverse agonist 7h. To further reveal the molecular mechanisms of different RORγt inverse agonists, we performed molecular dynamics simulations and found that “short” or “long” inverse agonists led to different behaviors of helixes H11, H11’, and H12 of RORγt. The “short” inverse agonist 6 destabilizes H11’ and dislocates H12, while the “long” inverse agonist 7h separates H11 and unwinds H12. The results indicate that the two types of inverse agonists may behave differently in downstream signaling, which may help identify novel inverse agonists with different regulatory mechanisms.

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.